Title: 20 Best B&B in Winchester, VA - Bed and Breakfast from $156 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx6056879)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.com/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d6056879.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/6e95af26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/480b5c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Windsor Suite) | Deep soaking bathtub](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/c20a2340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/df92df6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glen Gordon Manor [](https://www.expedia.com/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) Huntly 9.8/10 Exceptional (96 reviews) "Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander and Judith $299 nightly $327 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/7b9d69e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Overlook) | Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/8ab65f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/f0afdbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/80e06b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillbrook Inn [](https://www.expedia.com/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) Charles Town 8.6/10 Excellent (674 reviews) "Wonderful staff, and fall cottage was lovely." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henrik $178 nightly $197 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) ![Garden view](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/f6325d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/2db74ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/f3c32a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/098eec3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loudoun Valley Manor [](https://www.expedia.com/Waterford-Hotels-Loudoun-Valley-Manor.h36132129.Hotel-Information) Waterford 9.6/10 Exceptional (283 reviews) "Beatiful Location Reasonable Rates Great Breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Albert $136 nightly $156 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Waterford-Hotels-Loudoun-Valley-Manor.h36132129.Hotel-Information) ![Hallway](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/8659900e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/0869608f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/3be58fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/0932b9ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Evergreen [](https://www.expedia.com/Haymarket-Hotels-Inn-At-Evergreen.h15733502.Hotel-Information) Haymarket 9.4/10 Exceptional (133 reviews) "Beautiful property and excellent food." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paula $233 nightly $265 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Haymarket-Hotels-Inn-At-Evergreen.h15733502.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/f4cdce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed, Hot Tub, Garden View | 1 bedroom, premium bedding, pillowtop beds, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/686105c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/5afc8cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/827ae686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Manor Boutique Inn [](https://www.expedia.com/Lovettsville-Hotels-Stone-Manor-Boutique-Inn.h16281705.Hotel-Information) Lovettsville 9.6/10 Exceptional (97 reviews) "The breakfast was fabulous and the room great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MICHEL $213 nightly $243 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Lovettsville-Hotels-Stone-Manor-Boutique-Inn.h16281705.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/ff8b2dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/0a4c6df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/e770d74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/1f81d6e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Van Gogh Room in Villa [](https://www.expedia.com/Purcellville-Hotels-The-Van-Gogh-Room-In-Villa.h34090623.Hotel-Information) Purcellville 9.0/10 Wonderful (67 reviews) "Quiet setting and friendly owner." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen W. $339 nightly $386 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Purcellville-Hotels-The-Van-Gogh-Room-In-Villa.h34090623.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/a14a8657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/4272811e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living room](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/f7ffda1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/3abc3b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cantuta Inn [](https://www.expedia.com/Martinsburg-Hotels-Cantuta-Inn.h18669467.Hotel-Information) Harpers Ferry 9.0/10 Wonderful (76 reviews) "The hostess and her husband were friendly and made us feel very welcome! Breakfast was scrambled eggs with fruit and was nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron $165 nightly $185 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Martinsburg-Hotels-Cantuta-Inn.h18669467.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/7918f369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/4ee27c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/8d2e7c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/2f491ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Grass Roots Hill [](https://www.expedia.com/Purcellville-Hotels-The-Inn-At-Grass-Roots-Hill.h117723633.Hotel-Information) Purcellville 9.4/10 Exceptional (8 reviews) "House and property are absolutely beautiful. Staff are amazing and super friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chad $459 nightly $523 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Purcellville-Hotels-The-Inn-At-Grass-Roots-Hill.h117723633.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/8458539f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/9df5645f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/fdad32ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/1a36bdf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gay Street Inn [](https://www.expedia.com/Washington-Hotels-Gay-Street-Inn.h26679788.Hotel-Information) Washington 10/10 Exceptional (34 reviews) "Beautiful historic Inn with incredible owners and service. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee $359 nightly $387 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Washington-Hotels-Gay-Street-Inn.h26679788.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/a8e8b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/e996c5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/3b25e32e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Balcony | Balcony](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/f1d7b990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hopkins Ordinary Bed Breakfast and Ale Works [](https://www.expedia.com/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information) Sperryville 9.8/10 Exceptional (32 reviews) "Great place. Good food, great beer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phil $289 nightly $316 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/78704f31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/e0f66792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/957e6eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/aafbdad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view. [](https://www.expedia.com/Purcellville-Hotels-Monet-HoneymoonSuite-Elegant-Lrg-2rm-Wbalcony-In-VillaMountnpasture-Pool-View.h34329573.Hotel-Information) Purcellville 9.8/10 Exceptional (37 reviews) "Beautiful location, quiet, and Maud is a wonderful person." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis G. $419 nightly $478 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Purcellville-Hotels-Monet-HoneymoonSuite-Elegant-Lrg-2rm-Wbalcony-In-VillaMountnpasture-Pool-View.h34329573.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/30ef090b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Sunrise Room | Individually decorated, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/7a2a968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/0f03a335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/52d84062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Inn B&B [](https://www.expedia.com/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) Charles Town 9.6/10 Exceptional (442 reviews) "Excellent accommodations and breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William $163 nightly $185 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/03c5456b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/acb4aae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/e3ef8a74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video library](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/c0a1b19d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-Bird-Nest-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186918.Hotel-Information) Berkeley Springs 10/10 Exceptional (3 reviews) "Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel F. $266 nightly $295 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-Bird-Nest-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186918.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/1efbf58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/9e11ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/7def0784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/7243fdc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event [](https://www.expedia.com/Lovettsville-Hotels-Stone-Manor-Boutique-Inn-Country-Manor-With-Breathtaking-Gardens-And-Event.h63853807.Hotel-Information) Lovettsville 10/10 Exceptional (1 review) "Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lukas D. $13,007 nightly $15,403 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Lovettsville-Hotels-Stone-Manor-Boutique-Inn-Country-Manor-With-Breathtaking-Gardens-And-Event.h63853807.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/57d635cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/44858f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boudoir King Suite | In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/ccee4579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/36000000/35230000/35223100/35223045/c12f5cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn of the Shenandoah [](https://www.expedia.com/Luray-Hotels-Inn-Of-The-Shenandoah.h35223045.Hotel-Information) Luray 9.8/10 Exceptional (40 reviews) "It was an awesome place to stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eileen $303 nightly $364 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Inn-Of-The-Shenandoah.h35223045.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/2000000/1540000/1534000/1533986/fbc43f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1540000/1534000/1533986/0e1fba6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1540000/1534000/1533986/4ef0ca4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1540000/1534000/1533986/f52e4ba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mayneview B&B [](https://www.expedia.com/Luray-Hotels-Mayneview-BB.h1533986.Hotel-Information) Luray 8.2/10 Very Good (416 reviews) "We came to Lurray to see fall foliage and explore the caverns but the real star of our stay was this B&B. What an amazing experience! Gregory was the sweetest human and a great coversationalist. There is a lot of love that has gone into maintaining this old house and it shows. They have crafted a wonderfully curated experience from start to finish. We enjoyed hot chocolates by the fire pit, excellent balanced breakfasts, and a very comfortable king bedroom. 10/10!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha $224 nightly $258 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Mayneview-BB.h1533986.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/e5fc9b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/15a3d4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video library](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/bcee6e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/88ea5471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186922.Hotel-Information) Berkeley Springs 10/10 Exceptional (3 reviews) "My partner and I have both stayed in some pretty high end hotels and we were so impressed!! By far the best VRBO i’ve stayed in-newly renovated and decorated. You don’t want to pass up this hidden gem convenient to everything in Berkeley Springs!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deirdre A. $276 nightly $307 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186922.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/6f6e84c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/b98f28d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/9b2c5d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video library](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/7c9f1c3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Appalachian Suite In Town!- The Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186920.Hotel-Information) Berkeley Springs 10/10 Exceptional (2 reviews) "We loved the spot and will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Seth W. $279 nightly $310 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186920.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/9485d69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/b4a25399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video library](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/ac634e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/bafd7590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 50's Drive-In Inside the Grand Castalian Inn B&B [](https://www.expedia.com/Berkeley-Springs-Hotels-50s-Drive-In-Inside-The-Grand-Castalian-Inn-BB.h108011538.Hotel-Information) Berkeley Springs $292 nightly $324 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Berkeley-Springs-Hotels-50s-Drive-In-Inside-The-Grand-Castalian-Inn-BB.h108011538.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-23&endDate=2026-03-24®ionId=6056879&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_6056879) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg) ### Sleep Inn & Suites Winchester near University 2/10 Terrible "Killed a " [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/c1c4db32_y.jpg) ### Hampton Inn Martinsburg 8/10 Good "The door was sticking when it was opened & closed to our room. I could see that there was water damage to the ceiling. I feel there should be a fan in the bathroom. The young lady at the front desk at check in was very nice and courteous to me while checking in. Even when we came back to our room I requested another bottle of water, she graciously provided. The gym was very good, and gave us what was needed. The breakfast was fair, but again we were able to get what was needed. Fruit would be a nice addition." [](https://expedia.com/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "The hotel was conveniently located in town, even for a guest without a car on hand! Staff was AMAZING! Breakfast was solid and on time! Clean rooms and easy to navigate. " [](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Lansdowne Resort and Spa](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_y.jpg) ### Lansdowne Resort and Spa 10/10 Excellent "I have stayed at Landsdowne many years, typically for girls spa weekends or overnight stay while I’m in town. The Spa Experience is always phenomenal. The staff is friendly all around. I continue to enjoy my stays!" [](https://expedia.com/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Clean rooms." [](https://expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "very nice hotel,very clean" [](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/e7acb022_y.jpg) ### Hilton Garden Inn Dulles North 2/10 Terrible "The TV didn’t work. " [](https://expedia.com/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/bcd21d29_y.jpg) ### Best Western Leesburg Hotel & Conference Center 6/10 Okay "Safe but no hot water. " [](https://expedia.com/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) ![Fairfield Inn & Suites by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/0de00556_y.jpg) ### Fairfield Inn & Suites by Marriott Winchester 10/10 Excellent "Breakfast hot and fresh" [](https://expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 2,378 | | ----------------- | ------- | | Accommodation | 34 B&B | | Lowest Price | $156 | | Highest Price | $15,403 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Winchester? ### When is the best time to book a Bed and Breakfast in Winchester? > September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine. > > > For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter. ### What is the difference between a Winchester Bed & Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Restaurants.0-n6164092-0-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [Casino Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Casino-Hotel.0-n6164092-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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[Flights from Jacksonville (JAX) to Winchester (WGO) ](https://www.expedia.com/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Tampa (TPA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/tpa/wgo/tampa-to-winchester) - [Flights from Kansas City (MCI) to Winchester (WGO) ](https://www.expedia.com/lp/flights/mci/wgo/kansas-city-to-winchester) - [Flights to Winchester Regional ](https://www.expedia.com/Cheap-Flights-To-Winchester-Regional.d6033090.Travel-Guide-Flights) - [Flights from Minneapolis (MSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/msp/wgo/minneapolis-to-winchester) - [Flights from Cincinnati (CVG) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cvg/wgo/cincinnati-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Grand Rapids (GRR) to Winchester (WGO) ](https://www.expedia.com/lp/flights/grr/wgo/grand-rapids-to-winchester) - [Visit Old Town Winchester ](https://www.expedia.com/Winchester-Old-Town-Winchester.dx6164092) - [Bright Box Theater ](https://www.expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) - [Shenandoah Valley Discovery Museum ](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) - [George Washington's Office ](https://www.expedia.com/George-Washingtons-Office-Old-Town-Winchester.d6164042.Vacation-Attraction) - [Mt Hebron Cemetery ](https://www.expedia.com/Mt-Hebron-Cemetery-Winchester.d553248621532661845.Vacation-Attraction) - [Patsy Cline Historic House ](https://www.expedia.com/Patsy-Cline-Historic-House-Winchester.d553248621532661841.Vacation-Attraction) - [Museum of the Shenandoah Valley ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Abram's Delight ](https://www.expedia.com/Abrams-Delight-Winchester.d553248621532661839.Vacation-Attraction) - [Nalls Farm Market ](https://www.expedia.com/Nalls-Farm-Market-Winchester.d553248621532661846.Vacation-Attraction) - [Shenandoah University ](https://www.expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction) - [Rock Harbor Golf Course ](https://www.expedia.com/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction) - [Car rentals near Old Town Winchester ](https://www.expedia.com/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide) - [Car rentals near Patsy Cline Historic House ](https://www.expedia.com/Car-Rentals-In-Patsy-Cline-Historic-House.d553248621532661841.Car-Rental-Guide) - [Car rentals near Nalls Farm Market ](https://www.expedia.com/Car-Rentals-In-Nalls-Farm-Market.d553248621532661846.Car-Rental-Guide) - [Car rentals near Shenandoah University ](https://www.expedia.com/Car-Rentals-In-Shenandoah-University.d6127311.Car-Rental-Guide) - [Van Car Rentals near Shenandoah University ](https://www.expedia.com/Van-Car-Rentals-In-Shenandoah-University.d6127311-tVan.Car-Rental-Guide-Class) - 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